Ethyl 4,6-dichloropyridazine-3-carboxylate → ethyl 4-(6-(1H-pyrazol-1-yl)pyridin-2-ylamino)-6-chloropyridazine-3-carboxylate

HRID 1396445

Reaktionsgleichung

Reaktionsgleichung von HRID 1396445
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[N:4][C:3]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].[N:14]1([C:19]2[N:24]=[C:23]([NH2:25])[CH:22]=[CH:21][CH:20]=2)[CH:18]=[CH:17][CH:16]=[N:15]1>C(#N)C>[N:14]1([C:19]2[N:24]=[C:23]([NH:25][C:2]3[CH:7]=[C:6]([Cl:8])[N:5]=[N:4][C:3]=3[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:22]=[CH:21][CH:20]=2)[CH:18]=[CH:17][CH:16]=[N:15]1

Komponenten

4

Edukt 2

HCID 53428795Ethyl 4,6-dichloropyridazine-3-carboxylateHCID 665204692-Amino-6-(1H-pyrazol-1-yl)pyridine

Produkt 1

HCID 86689786ethyl 4-(6-(1H-pyrazol-1-yl)pyridin-2-ylamino)-6-chloropyridazine-3-carboxylateAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of ethyl 4,6-dichloropyridazine-3-carboxylate (230 mg, 1.04 mmol) and 6-(1H-pyrazol-1-yl)pyridin-2-amine (332.3 mg, 2.07 mmol) in acetonitrile (11.8 mL) was heated at 130° C. in a sealed tube for 48 h, then cooled concentrated in vacuo and then purified by chromatography (silica, Analogix 24 g RediSep Gold column 0 to 20% acetone in dichloromethane, 20 min) to give ethyl 4-(6-(1H-pyrazol-1-yl)pyridin-2-ylamino)-6-chloropyridazine-3-carboxylate (107 mg, 258 μmol, 25%) as a white solid. This material was 83% pure and was used directly in the next step without further purification. MS (EI/CI) m/z: 345.1 [M+H].

Aufarbeitung

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. custompurified by chromatography (silica, Analogix 24 g RediSep Gold column 0 to 20% acetone in dichloromethane, 20 min)

Quellen und Nachweise

ORD-Eintrag
ord-55ea6ac7063b4672acfe0ed385a31610
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901124B2

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